Author’s Note: This is another of my Jane Thompson ‘what if’ stories that’s been hounding me night and day, demanding it be written. The issues within this story are much darker than in any of my previous stories, told by a seventeen-year-old boy who witnessed the horrible treatment of the children by two families, if said children made it known they would not participate in any forced marriage. Reader beware, while what takes place is not told in great detail, it nevertheless can be disturbing. Also, there are flashbacks throughout the story, which may seem a bit confusing at times. ~ Jamie Lee ~

The Webster and Dorman families were brought together by the rescues first by a Dorman young man of a Webster young girl, then two years later a Webster young man of a Dorman young girl, and ensuing love which led to marriage when they each turned eighteen. Because of the first two marriages, other marriages, because of love, occurred between the Webster and Dorman families. But a little over one hundred and fifty years later, the then head of the Webster and Dorman families believed everything told of those first marriages to be lies. They were lies because no one married because of love, only opportunity, so those first two marriages had to have been forced. And it was at that point the love that had blossomed as a result of two rescues, that had brought two families together, was perverted, and a little over one hundred years of hell began for the two families. A hell that was Family Punishment for any Webster or Dorman child who failed to comply with the Family Obligation of marriage when they turned eighteen. And love be damned.

Seventeen-year-old Stephen William Webster and his nanny, Better Wilcox, finally blow the whistle after the murder of thirteen-year-old Rachael Dorman because she refused to be forced into a loveless marriage. Stephen and Betty must be hidden because people from the Webster and Dorman families are hunting him, thinking he is running away from a forced marriage. Betty makes contact with three of her former University sorority sisters, and together they formulate plans to hide Stephen at the one place unknown to either the Webster or Dorman families, the Winsome Girls’ School for Wayward Boys. Jane Thompson’s home.

“The four of us, me, Jane, Betty, and another I won’t name for your own safety, had hoped you would decide to explore your feminine side in order to help keep yourself safe. I’ve known what Jane does here for some time, and it starts by forcing the boys to begin their experiences by giving them no choice but to put on girls’ clothing. To do that,” and she points to the robe lying over the back of the chair, “their male clothes disappear and they either go see Jane naked or wear that robe. They also choose to be naked under that robe or wear a pair of panties. In your case, Stephen, everything you brought with you, including the clothes and shoes you have on, will be used by the gentleman you met today. He is the same height and build as yourself, so there won’t be any problems. So you’ll need to undress before you go into the bathroom, and take a pair of panties with you. If you like, I can explain the different types in those drawers, but it’s left up to you which style you choose.” Venessa then waited for Stephen to decide.

Stephen dropped his head and chuckled. “I think it best if you explain each style.” And here he smirked when he said, “After all, this will be the first time I’ve gotten into a girl’s panties.” It took less than the blink of her eyes for Venessa to understand what Stephen just said. She slaps him playfully on the arm before laughing out loud with him. Then she looks at him for a moment before saying, “Stephen William Webster, if I were a few years younger I’d hunt you down and drag you home to meet my parents. You’re going to be quite the catch for some girl one day.” She lightly slaps him on his leg and tells him, “C’mon, let’s go talk panties.”

After Venessa explains each style of panty in those drawers, Stephen makes his choice of a high cut brief in blue, and then walks back to the bed and sits down. He bends down and starts untying his shoes, taking off first the right one then the left. He sets them aside before removing the socks, placing one in each shoe. While sitting down he unbuttons his shirt and removes it, folding it before setting it on the bed. He then looks up at Venessa, who had been watching him this whole time. “Um...are you going to watch while I take everything else off,” he asks Venessa as she stands up. All Venessa says, as she’s turning around, is, “Boys! As if we women don’t know what you keep in your pants.” She’s hit in the back of the head by a pillow, before she hears the bathroom door close and the shower start. She chuckles to herself, as she bends to pick up the pillow. She gathers up everything and goes to do laundry; all but the underwear needs cleaned before she creates another Chester Thorton tomorrow.

Because of everything Stephen must remove, it takes about an hour before he shuts off the hair dryer and emerges from the bathroom. He’s startled after opening the door to find Jane sitting on the bed, waiting for him. She’s finally able to see the real Stephen William Webster and like what she sees, even the blue high cut briefs she’s wearing. Jane starts off teaching Stephen how to be a girl by saying, “Stephen, that bulge in the front of those panties will cause people to look at you strangely when you are dressed as a girl. I will save you the embarrassment by having you go back into the bathroom and tuck your penis back between your legs. And carefully push your testicles up into your body. I think you will then find those panties will fit better. Had you been one of the boys sent to me, I would have had you do it in front of me. Now go!” Jane had to hold back a chuckle because of the expression on Stephen’s face from what she just told him. But when he came back out those panties did fit much better.

“Now, a girl does not go around others just wearing her panties, so you can wear that robe for now.” When Stephen had put on the robe, Jane patted a spot on the bed besider, silently telling Stephen to sit beside her. Jane watches as Stephen sits down beside her, then tells him, “Before you sit down, whether wearing a robe, skirt or dress, always sweep the back of the garments towards your legs before you sit down. It not only keeps the garment from getting wrinkled, but helps with modesty. Try sitting down again.” She watches as Stephen stands up, sweeps the back of the robe towards his legs before sitting down. Legs spread apart. Jane reaches over and pushes his legs together, before telling him, “If a girl sits like that she will have every male within viewing distance looking up her dress or skirt. Keep your legs together unless you’re wearing pants, which you will never be doing while you are here. You can also cross your ankles with your knees together, or cross your legs as you see mine are crossed.” Jane watches as Stephen looks at her legs then tries to cross his to match hers.

Jane reaches over and gently takes Stephen’s chin and turns his head to face her. She looks him directly in the eyes and says, “Understand, Stephen, I will correct every mistake you make while learning to be a young lady. But I am doing it because I want to keep you safe. In the short time I have known you, I can see you have so much to offer this world. And I want to help you do that one day.”

Stephen reaches up and wipes his eyes before telling Jane, “I wouldn’t be addressing you as Aunt Jane if I didn’t think you had my welfare at heart. Besides Betty, you are the third person who’s cared about my life. And I will never forget you for all you’re doing.” Stephen reaches up and wipes off a tear that was sliding down Jane’s cheek, before she takes his hand and says, “There’s one other garment you must get used to. Follow me and I will explain that one to you.” They stand up together, then Jane has him remove the robe before taking his hand again and leading him back to the chest of drawers. She opens one drawer and begins to explain the different styles of bras that drawer contains. She does the same for the next drawer. She also explains what ‘chicken fillets’ are for, and notices how Stephen’s face has taken on a lovely pink shade. Jane opens the middle drawer of the vanity and takes out a tape measure, and uses it to measure Stephen from head to toe. Venessa gave Jane a rough guess of Stephen’s chest measurements, so the drawers contained bras which he might comfortably wear. Jane picked out a basic bra, in blue to match his panties, and taught him how to put in on. She then took out a pair of breast forms, showed him how to place them in each cup, stood back and saw the beginnings of a young girl. A young girl who had nice ‘B’ cup breasts; Sandy or Carolyn would glue on prosthetics tomorrow at the salon. Jane hoped when they went to the salon tomorrow, Stephen would be able to endure what they would do to him. But he was born into hell and came out the other side, so a little bit of salon work shouldn’t bother him.

Jane then had Stephen follow her to the closet, where she provides an explanation of every dress hanging from the racks. She explained the style, the parts of the dress, when it could, and should, be worn, and the fabric used to create each dress. She then proceeded to the shoes, showing him the difference between heel heights, designs and the name given for each style. She even gave him a crash course in fashion, what dress would go with which pair of shoes, what could be worn to accessorize the outfit, and what should never be worn together. She then had him pick out a dress that would be appropriate to wear around the house when guests were present. Jane was happy that Stephen had been listening to everything she’d told him, for he picked out a dress which wasn’t too dressy but would present a lovely young girl. He also picked out a pair of ivory flats, which would complement the dress nicely.

Dress and shoes were taken out of the closet, just as there was a knock on the bedroom door. Jane opened the door and let Venessa into the bedroom; Jane and Venessa had everything planned out. Plus, Venessa had been watching everything shown on a monitor sent from the hidden camera in the bedroom. When Venessa walked into the bedroom and saw Stephen, she whistled, and again told him she wished she was his age again so she could take him home to daddy. Both women chuckled as Stephen’s face again took on that lovely pink shade. But he held his demeanor, he didn’t shy away because two adult women saw him in a bra and panties.

Jane had him follow her to the chest of drawers, again, and opened another drawer before she began to explain about the different types of slips that drawer contained. As she did with the dresses, she told him when they should be worn and with what type of dress. She took out a white slip, one she knew would be right for the dress Stephen picked, and had Stephen put it on, showing him how to adjust the straps. The next part both women found rather comical, as Jane had Stephen put on the dress and told him to zip up the zipper on the back of the dress. Both women covered their mouths, as Stephen gyrated this way and that to pull up the zipper. Seeing Stephen start to get frustrated, Jane took pity on the boy and showed him an easy way for him to get it done. She then unzipped the dress several times, as Stephen practiced zipping it up several times.

Venessa then took Stephen’s hand and led him to the vanity, where she had him sit down before turning on the lights on either side of the vanity’s mirror. “It might take time for you to learn how to do this properly, but properly applying makeup is something all girls learn at some point in their lives. They also learn how to style their hair for different occasions.” Venessa told Stephen all this as she opened draws and took out a curling iron, combs, brushes, and several different makeups. Jane tried to keep her ‘stern teacher’ face intact, but the look on Stephen’s face as Venessa started explaining everything, made it hard to do.

Venessa used the curling iron, combs and brushes, to give Stephen’s shoulder length hair more bounce and curl. Jane was sitting on the bed as Venessa started explaining each step she performed as she applied a light layer of makeup; Jane admired Stephen’s tolerance for something so foreign to him. When Venessa was finished, she had Stephen stand up and face her and Jane, who stood up from the bed and was now standing in front of Stephen, Venessa at her side. “So, Janie, what do you think?” It was Stephen’s turn to watch, and chuckle, as Jane slowly turned her head to look at Venessa before telling her in a rather cold voice, “You do remember how I hate that name, correct?” It shocked Stephen a bit as Venessa gave Jane a light kiss on the lips before she said, “Yeah, but I still love ya girl.” Jane just shook her head before breaking out in a big smile, and returned Venessa’s light kiss. There were some stories neither woman would tell about their days at that University.

Both women returned their examination of the new girl standing before them, with Jane saying, “Venessa, we have before us a very pretty young girl, with a boy’s name. Can young girls have boy’s names?” Venessa playing along, as they decided, said, “Well, yeah they can, but they are usually spelled differently.” Jane then looked at Stephen and asked, “Does this new young girl know of a name she’d like to be called?” As much as one name had affected Stephen as he told his story, Jane had a suspicion what name he’d choose. She was proven right when he said, “Rachael. Rachael Jane Baker.” About that time there was a knock on the bedroom door. Venessa being closer, opened it to find Jenny standing there. Jenny simply told the three, “Marie wanted me to tell all of you that supper is ready.” Jane schooled herself and replied, “Thank you, Jenny. Please tell Marie we will be down shortly.” And as Jenny had learned, “Yes, ma’am,” was her proper reply, before she turned and went back downstairs.

After Jenny left, Jane turned back to Rachael and asked her, “Well, Rachael, are you ready to face the world?” Jane and Venessa could see Rachael’s eyes glisten, when Jane called Stephen, Rachael. Tears never fell, but there was a catch in her voice as she told both women, “When Venessa first told me I’d make a lovely young girl, I believed then I’d never do something like this. But thanks to the two of you, I’m confident doing this and yes, Aunt Jane, I’m ready to meet the world. Plus, I’m hungry.” Both women walked over to Rachael and hugged her before each gave her more words of encouragement. Jane already had her sentries picked out when they would be out in public. Sentries no one would spot until it was too late. And hopefully they wouldn’t have to act.

Rachael follows Jane and Venessa out of the bedroom and down the stairs. They walk into the dining room, where they find everything on the table, plus the man, Marie, and Jenny standing behind the chairs around the dining room table. When Rachael walks into the room, Marie is the first to say, “Very nice, Rachael. Very nice indeed.” Rachael gives Marie a questioning look, only to have Marie point to her ears--Marie heard what name she gave herself. The man offers something more, as he walks over to Rachael, takes her hand, kisses the back of her hand, and tells her, “If only I were a young lad again. I agree, very nice.” It was Jenny who received ‘the Jane look’ after she happily screeched out, “I have a big sister now!” Rachael took some of the sting out of Jane’s look by walking over to Jenny, hugging her, and saying, “And I have a little sister now.” The three women watched the two young girls before looking at each other and nodding at each other. They had planned well after all. The three looked back at Rachael hugging Jenny, and the huge, real, smile on Jenny’s face. Something that had only started being seen since Stephen arrived. Since everyone was now at the table, everyone could be seated. The man helped seat Jane and Marie, while the girls seated themselves, Rachael remembering Jane’s admonishment about sweeping the back of her dress towards her legs before sitting.

As usual, Jane never let a meal go by without it being a learning session. Both girls were asked general questions about a variety of subjects, the man joining in now and then, enjoying the give and take during the discussions. When the meal was over, Jane said to Jenny, “Jenny, you and Rachael please help Marie clear the table and help her in the kitchen.” Jane had to treat Rachael as she did Jenny, at least in front of Jenny. She would have to talk with Rachael and make sure Jenny was kept ignorant as to the real reason Stephen was there, in order to try and keep Jenny safe.

Jane had no more told Jenny what to do then Jenny jumped up and excitedly told Rachael, “C’mon, I’ll show you what needs done.” Things slowed down a bit after Jane said, “Jenny, a young lady does not jump up from the table. You will sit down and stand up properly, young lady.” Rachael had to put her hand over her mouth in order to not laugh because of the look on Jenny’s face. Jane and Marie did the same. An unhappy Jenny sat down, then stood up, pushed her chair under the table, and said, “Sorry, Aunt Jane, I was just so excited to have a big sister I forgot.” Jane schooled her face as she said, “Then, Jenny, you must do better at remembering. And think about all the things that might have happened by your exuberant rising from the chair.” Jenny looked at Jane and nodded her head, she understood. As Jane and the man started to walk out of the dining room, Jane turned and told Rachael, “Rachael, when you are through helping in the kitchen I want to see you in the Library.” And like Jenny’s response, Rachael replied, “Yes, Aunt Jane.”

Once the dining room table was cleared, and Marie and the girls were in the kitchen, Jane walked back into the dining room and stood by the kitchen door, listening. What she heard from Jenny filled her with hope, as Rachael asked questions and Jenny excitedly answered the questions. There was a bit of sadness in Jenny’s voice when Rachael suggested the two go out on the property so Jenny could show her some of the plants. When Jenny came to ask her, and Jane knew she would, Jane would have to keep the hope and glee out of her face. She would have to have her ‘stern teacher’ face on when that time came.

Jane had walked back into the Library, finding Parker sitting on one of the couches enjoying a glass of wine. She had just poured herself a glass, sat down next to Parker, when there was a knock on the Library door. “Come in,” she said loud enough to be heard on the other side of the door, before the door opened and Rachael came into the room. “You wanted to see me, Aunt Jane?” Rachael asked before closing the Library door behind her, for Jenny’s sake. They had to keep up appearances in front of Jenny. Jane pointed to the other couch and watched as Rachael walked over to it, sweeping the back of her dress towards her legs before sitting down, keeping her knees together. “You did that quite well, Rachael. How are you feeling about all this?”

Jane took a sip of her wine as she waited for Rachael to answer. It was a short spell before Rachael told Jane, “Better than I expected at first. But I’ve a feeling things will be, different tomorrow?” Stephen knew this beginning as Rachael wasn’t all Jane was going to ask of him, he’d noticed several things about Jenny. And he was proven right when Jane answered with, “Yes, Rachael, tomorrow will be different. You and Jenny have an appointment at Marisha Chalet, the salon I use for my girls, where you will get a complete makeover, and several lessons. You have nothing to fear from Carolyn or Sandy, they know about you, and will help you learn about aspects of being a girl. If you have questions, ask while you are with each lady. Now one part might be a little uncomfortable, but must be done if you are to have a girly figure.” Jane and the man watched as Rachael did Stephen’s classic head drop and chuckle before saying, “A corset, right?” It was Jane’s turn to chuckle before replying, “Yes, a corset. The other part is getting your ears pierced, as most girls have these days.” The man chuckled this time as Rachael just shook her head at the thought of having to wear a corset and getting her ears pierced, something Stephen had never thought of doing.

“Rachael, there is something more serious we must discuss. In order to help keep you safe, you must be Rachael any time you are with Jenny. You must not tell her, or even hint at, the real reason you are here. While she may not say anything deliberately, she could accidentally blurt out something at the wrong time. Our plan was to have her think you were sent here just as she was sent, though explaining about Chester Thorton might be a bit problematic. I suppose you could tell her part of the truth, that some bad people were looking for you and the disguise was to keep you safe while traveling.”

“But for the rest of the evening, I would like you to sit with Jenny and continue talking with her, asking her questions, to help bring her out of that shell she has built around her. Her actions tonight after supper were a tremendous breakthrough, thanks to you and the way you treated her. Please, keep encouraging her to tell you about herself and her interests. Marie will notify you and Jenny when it is time for bed. Marie will go with you and tell you how to remove your makeup before you shower. She will also show you which moisturizer to apply to your face after showering. Wash your hair, and shave as you did earlier. In the bottom drawer of that chest of drawers you will find a selection of nighties you may choose from for tonight. You must also change your panties as well. Please leave the bra you are wearing on while you sleep, so you can get used to the feel of it on. In the morning, Marie will wake you and have you take a shower and shave. Fold up the nighties you wore and place in under the pillow after you make the bed. Put the bra and panties you wore to bed in the clothes hamper you will find in the closet.”

“Rachael, I realize all of this may be hard on you at first. But our intentions are to keep you safe, and we can only do that if you immerse yourself in being Rachael. If you seem like a boy dressed as a girl, people will notice faster than if you are Rachael any time you are around other people. Your voice, mannerisms, actions, all must be girl-like, or you will be outed. Go on now, take what time left before bed and talk with Jenny.” Jane and Parker were a bit surprised when Rachael replied in a more feminine voice as she said, “Yes, Aunt Jane,” before standing up, bidding the man a safe journey, and leaving the Library, closing the door behind her.

Parker had watched this boy go from Chester Thorton to Rachael Jane Baker with ease. He had observed her over supper, how she interacted with Jenny, her mannerisms during supper, and now as she came into the Library, talked with Jane, then left the Library. Parker told a worried looking Jane, “He’s going to be alright, Jane. He’s a born actor,” and as he put an arm around her shoulders she replied, “I hope you’re right, Parker, I hope you’re right.” Jane laid her head on Parker’s shoulders, and he felt his shirt get wet where Jane’s head lay. “Aunt Jane,” he began, “the entire time I was with you, and helped be the senior girl, I never saw a boy take on their female persona quicker than that boy. And he’s done it voluntarily and, unlike myself, and I deem others, never fought you on it. Plus, Jane, his voice, his mannerisms, all suggest he’s been a girl his entire life. No one will see that young man as anything but a young girl.” Jane chuckled at the memory when Parker first came to her, and the fits he threw. But she knew he was right in everything he just said, Stephen does seem to have been a girl his entire life. “Parker, perhaps she does act like a girl due to having an IQ not too many points below 200, and an eidetic memory. Perhaps both of these help him take on any role he requires in order to survive. Remember, there are a lot of unpleasant memories stored in that mind, so there had to be a way for him to stay sane and alive at the same time. Had he betrayed anything at any time, he wouldn’t be here now, Parker. He’d be dead.”

The two were quiet for some time, thinking about what the other said, before finishing their wine and deciding they too should go to bed. Jane walked Parker out of the Library, bid him a good night, before going into the Study and checking on Jenny, finding her sound asleep. Rachael was a different matter, though, as Jane heard her asking herself questions about being Rachael. “I’m actually comfortable being Rachael. Does that mean I’m really a girl or secretly wanting to be a girl? Can I actually be Rachael out in public? I wish, above all, I knew the answers. I’m scared it all might actually be true.” Jane watched as Rachael wiped tears off her cheeks, before turning out the light and climbing into bed. ‘Yes, Rachael,’ Jane thought, ‘that is something which needs to be discovered.’ She shut everything down, the alarm in her bedroom would alert her if there was trouble with the girls, got up out of the desk chair and made her way to her bedroom after closing the Study door. Stephen’s admissions today had drained her.

The next morning started as Jane had told Rachael. Only Rachael was ahead of the ‘game’ as Marie found out when she went to wake Rachael after waking Jenny. When Marie walked into Rachael’s bedroom, Rachael’s bed was already made and clothes were already laid out on the bed. As Marie listened, she could hear a beautiful voice singing about the running shower. She listened for a while before knocking on the bathroom door, opening it and asking, “Is everything alright, cher?” As she waited for an answer, she looked around the bathroom, spotting the lingerie lying on the toilet seat lid. “Yes, Marie, I’m fine, so far. I made sure to shave my face and under arms twice, and I’m using a hair remover on my legs right now. Um...are the bra and panties I selected suitable, they’re laying on the toilet seat lid.” Marie had to smile after all she heard, and did agree with the selection of bra and panties. “Yes, cher, the selection is perfect, as is the dress and accessories you chose. If I might ask, cher, you are up early, no. Is this your habit before here?” The water shut off, and the shower curtain pulled back, before Rachael said, “Honestly, Marie, I was excited to start the day. After talking with Aunt Jane yesterday, and being open with someone besides Betty, I feel a great burden has been lifted from my shoulders.”

Rachael was totally naked, as she dried herself in front of Marie with a bath towel. “Did Aunt Jane tell you anything about what I told her, even the parts that were hard to tell?” Rachael saw the sad face Marie made as she said, “Yes, cher. She told me everything, even the hard parts.” She reached up and wiped a tear off her cheek before saying, “Come, we have to get you ready for the day.” Marie was surprised when a very naked Stephen walked up to her, kissed her on the cheek and told her in perfect French, “Merci beaucoup, ma tante,” before pulling on the panties, tucking his manhood back between his legs. Marie had to wipe her eyes again. Rachael then picked up the bra and this time with deft fingers, put her arms through the straps, and reached around behind her and hooked the bra ends together. Marie only quirked one eyebrow this time.

She had Rachael wait to put on the dress, until her hair and makeup were done, suggesting a slip be worn with the dress Rachael chose, and showing her which one would be best. Marie had Rachael sit in front of the vanity mirror, after she had put the slip on, before telling Rachael to do her makeup in order to see what she learned from the previous day. A short time later, a surprised Marie stared into the mirror as a very beautifully made up Rachael was reflected in the mirror; Jane was also going to be surprised how well Rachael did putting on her makeup today. Being able to see one’s face is different than doing one’s hair, but Rachael did manage to make her hair very presentable after it was dried; a few more lessons and it would be perfect.

Rachael then put on her knee high socks, then her dress. Marie had to suppress a chuckle as Rachael was still having trouble zipping up the zipper. But she persevered, and was finally able to pull up the zipper. She slipped on her shoes, flats this time and she and Marie headed down to the dining room for breakfast. Marie followed behind to watch how Rachael walked. She quirked an eyebrow as she saw that Rachael was walking as a girl would walk, something a boy shouldn’t be able to do without lessons. She’d have to tell Jane about this. Either Stephen was a girl at heart, or an excellent actor.